Water → HCID 22734119, compound

HRID 1057896Notes

Reaction equation

[CH3:1][C:2]1([CH3:26])[CH2:6][C:5]2[C:7]([Sn](CCCC)(CCCC)CCCC)=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:4]=2[O:3]1.Br[C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:26][C:2]1([CH3:1])[CH2:6][C:5]2[C:7]([C:28]3[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=3)=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:4]=2[O:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution (30 ml) of Compound 144a obtained in Step A in DMF was added to a mixture of methyl 4-bromobenzoate (1.67 g), palladium acetate (0.18 g), sodium carbonate (2.10 g), and dimethylformamide (DMF) (70 ml), followed by stirring at 80° C. for one hour. A small amount of water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/20) to give Compound 144 (1.35 g, 55.6%) as colorless crystals.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with 1N hydrochloric acid
dry with materiala saturated saline and dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/20)

Sources & evidence

ORD record: ord-936338734f1c424fb9cdbaf8f5a06659
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514996B2

Reaction notes

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